CA2822016C - Synthese a basse temperature de chlorhydrate de methylphenidate - Google Patents

Synthese a basse temperature de chlorhydrate de methylphenidate Download PDF

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Publication number
CA2822016C
CA2822016C CA2822016A CA2822016A CA2822016C CA 2822016 C CA2822016 C CA 2822016C CA 2822016 A CA2822016 A CA 2822016A CA 2822016 A CA2822016 A CA 2822016A CA 2822016 C CA2822016 C CA 2822016C
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CA
Canada
Prior art keywords
degree
molar equivalents
reaction temperature
acid
ratio
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Expired - Fee Related
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CA2822016A
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English (en)
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CA2822016A1 (fr
Inventor
C. Frederick M. Huntley
Knicholaus Dudley La Lumiere
Helge Alfred REISCH
Erik Wayne Kataisto
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Rhodes Technologies Inc
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Publication of CA2822016A1 publication Critical patent/CA2822016A1/fr
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Publication of CA2822016C publication Critical patent/CA2822016C/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention porte sur un procédé pour la préparation de chlorhydrate de méthylphénidate. Le procédé comprend l'estérification d'acide ritalinique et de méthanol en présence d'un catalyseur acide à une basse température. Le procédé peut éventuellement comprendre l'ajout d'un orthoester.
CA2822016A 2010-12-17 2011-12-16 Synthese a basse temperature de chlorhydrate de methylphenidate Expired - Fee Related CA2822016C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201061424424P 2010-12-17 2010-12-17
US61/424,424 2010-12-17
PCT/IB2011/003140 WO2012080834A1 (fr) 2010-12-17 2011-12-16 Synthèse à basse température de chlorhydrate de méthylphénidate

Publications (2)

Publication Number Publication Date
CA2822016A1 CA2822016A1 (fr) 2012-06-21
CA2822016C true CA2822016C (fr) 2016-10-25

Family

ID=45509554

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2822016A Expired - Fee Related CA2822016C (fr) 2010-12-17 2011-12-16 Synthese a basse temperature de chlorhydrate de methylphenidate

Country Status (14)

Country Link
US (1) US9475770B2 (fr)
EP (2) EP2937336A1 (fr)
JP (1) JP5886869B2 (fr)
KR (2) KR20150029769A (fr)
CN (1) CN103298785B (fr)
AU (1) AU2011342894C1 (fr)
BR (1) BR112013015072A2 (fr)
CA (1) CA2822016C (fr)
CO (1) CO6741202A2 (fr)
ES (1) ES2542433T3 (fr)
MX (1) MX343653B (fr)
NZ (1) NZ612298A (fr)
PH (1) PH12013501257A1 (fr)
WO (1) WO2012080834A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014024203A1 (fr) * 2012-08-07 2014-02-13 Zcl Chemicals Limited Procédé perfectionné pour la préparation de chlorhydrate de dexméthylphénidate
WO2014083572A1 (fr) * 2012-11-29 2014-06-05 Zcl Chemicals Limited Procédé de préparation de sels de l'acide d-thréo-ritalinique par le biais de nouveaux sels de son intermédiaire
EP3066075A1 (fr) * 2013-11-08 2016-09-14 Noramco, Inc. Procédé de préparation de méthylphénidate et de ses sels pharmaceutiques
CA2951072A1 (fr) * 2014-06-06 2015-12-10 Rhodes Pharmaceuticals, L.P. Methodes pour le traitement d'un trouble deficitaire de l'attention avec hyperactivite faisant appel a du methylphenidate
CA2936740C (fr) 2014-10-31 2017-10-10 Purdue Pharma Methodes et compositions destinees au traitement du trouble de deficit d'attention
CN104744342A (zh) * 2015-02-11 2015-07-01 河南中帅医药科技股份有限公司 盐酸右哌甲酯晶型及其制备方法
CN107325039B (zh) * 2016-04-29 2022-12-16 国药集团国瑞药业有限公司 一种盐酸右哌甲酯的制备方法
US10722473B2 (en) 2018-11-19 2020-07-28 Purdue Pharma L.P. Methods and compositions particularly for treatment of attention deficit disorder
CN110698341A (zh) * 2019-10-24 2020-01-17 安庆博曼生物技术有限公司 丙炔酸衍生物的环保制备方法

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2507631A (en) 1944-01-19 1950-05-16 Ciba Pharm Prod Inc Pyridine and piperidine compounds and process of making same
US2957880A (en) 1953-12-23 1960-10-25 Ciba Pharm Prod Inc Process for the conversion of stereoisomers
US2838519A (en) 1953-12-23 1958-06-10 Ciba Pharm Prod Inc Process for the conversion of stereoisomers
US4347374A (en) 1980-07-21 1982-08-31 Merck & Co., Inc. Acid addition salts of N-trityl-α-fluoromethylhistidine enantiomer derivatives
US5733756A (en) 1996-01-05 1998-03-31 Celgene Corporation Lactams and processes for stereoselective enrichment of lactams, amides, and esters
US6242464B1 (en) 1996-01-22 2001-06-05 Chiroscience Limited Single isomer methylphenidate and resolution process
GB9604943D0 (en) 1996-03-08 1996-05-08 Chiroscience Ltd Resolution
WO1998025902A1 (fr) 1996-12-13 1998-06-18 Medeva Europe Limited Preparation de threo-methylphenidate enrichi en un enantiomere
GB9700912D0 (en) * 1997-01-17 1997-03-05 Chiroscience Ltd Resolution
US5936091A (en) 1997-05-22 1999-08-10 Celgene Corporation Processes and intermediates for resolving piperidyl acetamide stereoisomers
US6548522B1 (en) 1999-10-12 2003-04-15 Hoffmann-La Roche Inc. Method for treating conditions related to the glutamate receptor using carboxylic acid amide derivatives
US7482366B2 (en) 2001-12-21 2009-01-27 X-Ceptor Therapeutics, Inc. Modulators of LXR
US20040242613A1 (en) 2003-01-30 2004-12-02 Boehringer Ingelheim Pharmaceuticals, Inc. Pyrimidine derivatives useful as inhibitors of PKC-theta
CH712083B1 (de) 2003-02-05 2017-07-31 Siegfried Ag Verfahren zur Herstellung von d-threo-2-Phenyl-2-piperidin-2-yl-essigsäureestern.
US20050032873A1 (en) 2003-07-30 2005-02-10 Wyeth 3-Amino chroman and 2-amino tetralin derivatives
US7229557B2 (en) 2004-02-04 2007-06-12 Konec, Inc. Method to separate stereoisomers
AU2007288124B2 (en) 2006-08-24 2013-04-04 Australian Nuclear Science & Technology Organisation Fluorinated ligands for targeting peripheral benzodiazepine receptors
US20100022446A1 (en) 2007-01-18 2010-01-28 Novo Nordisk A/S Use of Peptides in Combination with Surgical Intervention for the Treatment of Obesity
EP2376451A1 (fr) 2009-01-09 2011-10-19 Mallinckrodt LLC Synthèse du méthylphénidate et des analogues de celui-ci
WO2011067783A1 (fr) * 2009-12-01 2011-06-09 Harman Finochem Limited Procédé de préparation de chlorhydrate de phénidate de méthyle

Also Published As

Publication number Publication date
AU2011342894B2 (en) 2015-05-07
CN103298785B (zh) 2016-04-20
EP2651892B1 (fr) 2015-04-22
WO2012080834A8 (fr) 2012-09-13
AU2011342894A1 (en) 2013-05-02
US9475770B2 (en) 2016-10-25
KR20150029769A (ko) 2015-03-18
WO2012080834A1 (fr) 2012-06-21
EP2937336A1 (fr) 2015-10-28
KR20130115322A (ko) 2013-10-21
EP2651892A1 (fr) 2013-10-23
PH12013501257A1 (en) 2022-03-30
KR101561361B1 (ko) 2015-10-16
JP2014503530A (ja) 2014-02-13
CO6741202A2 (es) 2013-08-30
ES2542433T3 (es) 2015-08-05
NZ612298A (en) 2014-06-27
MX343653B (es) 2016-11-07
US20150038720A1 (en) 2015-02-05
CA2822016A1 (fr) 2012-06-21
MX2013007020A (es) 2014-11-10
AU2011342894C1 (en) 2015-07-30
JP5886869B2 (ja) 2016-03-16
CN103298785A (zh) 2013-09-11
BR112013015072A2 (pt) 2016-07-12

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